Ethyl bromoacetate → ETHYL 2-(1H-1,2,3-TRIAZOL-1-YL)ACETATE

HRID 2039467Notes

Reaction equation

HRID 2039467 reaction equation
[Na].[NH:2]1[CH:6]=[CH:5][N:4]=[N:3]1.Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(O)C>[N:2]1([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545SodiumHCID 178418936HCID 178418936, compound

Product 1

HCID 10103365ETHYL 2-(1H-1,2,3-TRIAZOL-1-YL)ACETATE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

129.2 g (5.6 mmol) of sodium are added slowly to 4.0 litres of ethanol. 400.0 g (5.6 mol) of 1,2,3-1H-triazole are then added, and 623 ml (938.2 g, 5.6 mol) of ethyl bromoacetate are added dropwise at an internal temperature of 20-25° C. The mixture is stirred at RT for 48 h. The precipitated solid is filtered off, the ethanol is removed under reduced pressure and the mixture is filtered again. The residue is taken up in ethyl acetate, filtered, again concentrated under reduced pressure and purified by distillation on a 30 cm column. The product is obtained at a bath temperature of 140° C., a head temperature of 60-115° C. and a pressure of 1 mbar. Yield: 440.0 g (50% of theory)

Workup

  1. filtrationThe precipitated solid is filtered off
  2. customthe ethanol is removed under reduced pressure
  3. filtrationthe mixture is filtered again
  4. filtrationfiltered
  5. concentrationagain concentrated under reduced pressure
  6. distillationpurified by distillation on a 30 cm column
  7. customThe product is obtained at a bath temperature of 140° C.
  8. customa head temperature of 60-115° C.

Sources & evidence

ORD record
ord-a564b797fb574755a8495d20b1dd5988
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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